ethyl 2-(7-methoxy-1-oxo-2,3,4,5-tetrahydro-1H-1-benzaepin-2-yl)-ethanoate | 159020-90-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(7-methoxy-1-oxo-2,3,4,5-tetrahydro-1H-1-benzaepin-2-yl)-ethanoate
• 英文别名: ethyl 2-(7-methoxy-1-oxo-4,5-dihydro-3H-2-benzazepin-2-yl)acetate
• CAS: 159020-90-3
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: UBUJTZIFJZHNJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(7-methoxy-1-oxo-2,3,4,5-tetrahydro-1H-1-benzaepin-2-yl)-ethanoate 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以69%的产率得到2-(7-methoxy-1-oxo-2,3,4,5-tetrahydro-1H-2-benzazepin-2-yl)ethanoic acid
  参考文献：
  名称：

  Design, Synthesis, and Opioid Receptor Binding of Some Novel Benzazepine Constrained Leucine Enkephalin Mimetics

  摘要：

  An N-substituted 2-benzazepine, previously reported to possess morphine-like analgesic activity in vivo, was adapted for use as a constrained mimic of the N-terminal residues of leucine enkephalin. Molecular modeling was used to evaluate the suitability of the 2-benzazepine nucleus for this purpose. The principle peptide constraint structure, 2-(7-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepin-2-yl)-ethanoic acid (8) and some structurally related benzazepine analogues were synthesized and incorporated into peptides using solid-phase protocols. Radioligand receptor binding studies were used to evaluate the general opioid receptor affinity of the target compounds. The target constrained peptide (21) demonstrated an affinity for [H-3]naloxone-labeled sites (IC50 16 mu M) comparable to the corresponding leucine enkephaline analogue. (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1024
• 作为产物：
  描述：

  7-甲氧基-2,3,4,5-四氢-1H-2-苯并氮杂卓-1-酮 、 溴乙酸乙酯 在 sodium hydride 作用下， 生成 ethyl 2-(7-methoxy-1-oxo-2,3,4,5-tetrahydro-1H-1-benzaepin-2-yl)-ethanoate
  参考文献：
  名称：

  Design, Synthesis, and Opioid Receptor Binding of Some Novel Benzazepine Constrained Leucine Enkephalin Mimetics

  摘要：

  An N-substituted 2-benzazepine, previously reported to possess morphine-like analgesic activity in vivo, was adapted for use as a constrained mimic of the N-terminal residues of leucine enkephalin. Molecular modeling was used to evaluate the suitability of the 2-benzazepine nucleus for this purpose. The principle peptide constraint structure, 2-(7-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepin-2-yl)-ethanoic acid (8) and some structurally related benzazepine analogues were synthesized and incorporated into peptides using solid-phase protocols. Radioligand receptor binding studies were used to evaluate the general opioid receptor affinity of the target compounds. The target constrained peptide (21) demonstrated an affinity for [H-3]naloxone-labeled sites (IC50 16 mu M) comparable to the corresponding leucine enkephaline analogue. (C) 1994 Academic Press, Inc.

  DOI：

  10.1006/bioo.1994.1024